1,1′-[(Biphenyl-4,4′-di­yl)bis­(methyl­ene)]di-1H-imidazol-3-ium tetra­chlorido­mercurate(II)

Wen, B.; Hou, G.-F.; Yu, Y.-H.; Gao, J.-S.

doi:10.1107/S1600536811047374

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page m1756

https://doi.org/10.1107/S1600536811047374

Open

access

1,1′-[(Biphenyl-4,4′-diyl)bis(methylene)]di-1H-imidazol-3-ium tetrachloridomercurate(II)

Bo Wen,^a Guang-Feng Hou,^a,^b Ying-Hui Yu ^a,^b and Jin-Sheng Gao ^a,^b ^*

^aCollege of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China, and ^bEngineering Research Center of Pesticides of Heilongjiang University, Heilongjiang University, Harbin 150050, People's Republic of China
^*Correspondence e-mail: hgf1000@163.com

(Received 3 November 2011; accepted 9 November 2011; online 12 November 2011)

In the title compound, (C₂₀H₂₀N₄)[HgCl₄], the Hg^II ion is four-coordinated in a tetrahedral environment defined by four chloride ions. The dihedral angle between the two phenyl rings is 32.83 (15)°. The protonated 1,1′-[(biphenyl-4,4′-diyl)bis(methylene)]di-1H-imidazol-3-ium cations, showing a cis conformation, link the [HgCl₄]²⁻ anions into an R₄⁴(42) motif via N—H⋯Cl hydrogen bonds.

Related literature

For the synthesis of the ligand, see: Zhu et al. (2002 ).

Experimental

Crystal data

(C₂₀H₂₀N₄)[HgCl₄]
M_r = 658.79
Monoclinic, P 2₁ /c
a = 8.9318 (18) Å
b = 15.347 (3) Å
c = 16.840 (3) Å
β = 92.62 (3)°
V = 2306.0 (8) Å³
Z = 4
Mo Kα radiation
μ = 7.15 mm⁻¹
T = 293 K
0.24 × 0.23 × 0.22 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.280, T_max = 0.306
22111 measured reflections
5260 independent reflections
3913 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.068
S = 1.03
5260 reflections
269 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.98 e Å⁻³
Δρ_min = −0.94 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H21⋯Cl1ⁱ	0.90 (1)	2.25 (2)	3.134 (5)	170 (7)
N4—H41⋯Cl3ⁱⁱ	0.90 (1)	2.45 (4)	3.168 (5)	137 (5)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z-{\script{1\over 2}}]$ ; (ii) $[x-1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811047374/hy2485sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811047374/hy2485Isup2.hkl

checkCIF report

Comment top

N-containing ligands with an arene center have been widely used as building blocks for constructing inorganic-organic supramolecular architectures. The title compound was synthesized at a low pH value condition, as an unexpected product during the process of preparing the ligand–Hg complex. Herein, we report its structure.

In the title compound, the Hg^II ion is four-coordinated in a tetrahedral environment defined by four Cl ions (Fig. 1). The protonated ligand shows a cis conformation, which links the [HgCl₄]^2- anions, forming a R₄⁴(42) motif via N—H···Cl hydrogen bonds (Fig. 2, Table 1).

Related literature top

For the synthesis of the ligand, see: Zhu et al. (2002).

Experimental top

The 4,4'-(dimethylenebiphenyl)diimidazol ligand was synthesized as the literature method (Zhu et al., 2002). HgCl₂ (0.140 g, 0.5 mmol) and the ligand (0.160 g, 0.5 mmol) were dissolved in 10 ml ethanol under stirring to get white deposit. 1M HCl solution had been dropped to adjust the pH value until the deposit dissolved. The obtained solution was allowed to stand for several days. Colorless crystals of the title compound were obtained (yield: 28%) as salt-type adducts of the protonated ligand and [HgCl₄]^2- anion.

Structure description top

For the synthesis of the ligand, see: Zhu et al. (2002).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids at the 50% probability level.
	Fig. 2. A partial packing view, showing the hydrogen-bonded R₄⁴(42) motif.

1,1'-[(Biphenyl-4,4'-diyl)bis(methylene)]di-1H-imidazol-3-ium tetrachloridomercurate(II) top

Crystal data top

(C₂₀H₂₀N₄)[HgCl₄]	F(000) = 1264
M_r = 658.79	D_x = 1.898 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 15195 reflections
a = 8.9318 (18) Å	θ = 3.3–27.5°
b = 15.347 (3) Å	µ = 7.15 mm⁻¹
c = 16.840 (3) Å	T = 293 K
β = 92.62 (3)°	Block, colorless
V = 2306.0 (8) Å³	0.24 × 0.23 × 0.22 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	5260 independent reflections
Radiation source: rotation anode	3913 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
ω scan	θ_max = 27.5°, θ_min = 3.3°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→11
T_min = 0.280, T_max = 0.306	k = −19→18
22111 measured reflections	l = −21→21

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.068	w = 1/[σ²(F_o²) + (0.0184P)² + 2.3484P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
5260 reflections	Δρ_max = 0.98 e Å⁻³
269 parameters	Δρ_min = −0.94 e Å⁻³
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00514 (18)

Crystal data top

(C₂₀H₂₀N₄)[HgCl₄]	V = 2306.0 (8) Å³
M_r = 658.79	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.9318 (18) Å	µ = 7.15 mm⁻¹
b = 15.347 (3) Å	T = 293 K
c = 16.840 (3) Å	0.24 × 0.23 × 0.22 mm
β = 92.62 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	5260 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3913 reflections with I > 2σ(I)
T_min = 0.280, T_max = 0.306	R_int = 0.046
22111 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	2 restraints
wR(F²) = 0.068	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.98 e Å⁻³
5260 reflections	Δρ_min = −0.94 e Å⁻³
269 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.1318 (11)	1.0186 (5)	−0.3528 (4)	0.117 (3)
H1	0.0501	0.9947	−0.3813	0.140*
C2	0.1321 (6)	1.0519 (4)	−0.2798 (3)	0.0855 (17)
H2	0.0506	1.0551	−0.2474	0.103*
C3	0.3553 (6)	1.0636 (3)	−0.3221 (3)	0.0712 (14)
H3	0.4566	1.0765	−0.3252	0.085*
C4	0.3225 (6)	1.1204 (3)	−0.1864 (3)	0.0621 (12)
H4A	0.2678	1.1743	−0.1795	0.074*
H4B	0.4280	1.1347	−0.1883	0.074*
C5	0.2996 (5)	1.0618 (3)	−0.1164 (2)	0.0489 (9)
C6	0.3775 (5)	0.9845 (3)	−0.1082 (2)	0.0494 (10)
H6	0.4405	0.9672	−0.1478	0.059*
C7	0.3633 (4)	0.9323 (2)	−0.0421 (2)	0.0433 (9)
H7	0.4160	0.8801	−0.0379	0.052*
C8	0.2708 (4)	0.9572 (2)	0.0182 (2)	0.0395 (8)
C9	0.1902 (5)	1.0336 (3)	0.0087 (2)	0.0517 (10)
H9	0.1257	1.0506	0.0476	0.062*
C10	0.2040 (5)	1.0850 (3)	−0.0577 (3)	0.0571 (11)
H10	0.1482	1.1360	−0.0631	0.068*
C11	0.2651 (4)	0.9048 (3)	0.0920 (2)	0.0409 (8)
C12	0.2847 (4)	0.8145 (3)	0.0914 (2)	0.0481 (9)
H12	0.2986	0.7860	0.0435	0.058*
C13	0.2837 (4)	0.7670 (3)	0.1610 (3)	0.0543 (11)
H13	0.2961	0.7069	0.1591	0.065*
C14	0.2648 (4)	0.8067 (3)	0.2333 (3)	0.0555 (11)
C15	0.2461 (5)	0.8959 (3)	0.2345 (3)	0.0575 (11)
H15	0.2340	0.9241	0.2827	0.069*
C16	0.2449 (4)	0.9439 (3)	0.1652 (2)	0.0507 (10)
H16	0.2303	1.0039	0.1674	0.061*
C17	0.2680 (5)	0.7536 (4)	0.3091 (3)	0.0738 (15)
H17A	0.3061	0.6957	0.2986	0.089*
H17B	0.3351	0.7809	0.3486	0.089*
C18	−0.0065 (5)	0.7105 (3)	0.3035 (3)	0.0578 (11)
H18	−0.0115	0.6846	0.2535	0.069*
C19	−0.1192 (6)	0.7189 (3)	0.3521 (3)	0.0702 (13)
H19	−0.2171	0.6996	0.3425	0.084*
C20	0.0762 (7)	0.7775 (3)	0.4100 (3)	0.0679 (14)
H20	0.1380	0.8065	0.4472	0.082*
Cl1	0.69235 (14)	0.46688 (7)	0.05336 (7)	0.0659 (3)
Cl2	0.58278 (14)	0.62872 (8)	0.22325 (7)	0.0724 (3)
Cl3	0.94394 (12)	0.67508 (8)	0.09563 (7)	0.0640 (3)
Cl4	0.58329 (12)	0.71468 (7)	−0.02401 (7)	0.0606 (3)
Hg1	0.67130 (2)	0.626552 (12)	0.089746 (11)	0.06180 (9)
N1	0.2722 (4)	1.0801 (2)	−0.26138 (18)	0.0456 (7)
N2	0.2709 (9)	1.0261 (3)	−0.3772 (3)	0.1021 (19)
H21	0.294 (8)	1.011 (5)	−0.4267 (18)	0.153*
N3	0.1169 (4)	0.7466 (2)	0.34045 (19)	0.0512 (8)
N4	−0.0658 (6)	0.7599 (3)	0.4169 (3)	0.0741 (12)
H41	−0.116 (6)	0.772 (4)	0.461 (2)	0.111*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.172 (8)	0.099 (5)	0.073 (5)	−0.059 (5)	−0.052 (5)	0.018 (4)
C2	0.072 (3)	0.117 (5)	0.067 (4)	−0.037 (3)	−0.011 (3)	0.019 (3)
C3	0.084 (3)	0.083 (3)	0.049 (3)	0.012 (3)	0.018 (3)	0.015 (3)
C4	0.088 (3)	0.055 (2)	0.043 (2)	−0.022 (2)	−0.006 (2)	0.005 (2)
C5	0.065 (3)	0.047 (2)	0.035 (2)	−0.010 (2)	−0.0025 (18)	0.0011 (17)
C6	0.058 (2)	0.059 (2)	0.032 (2)	−0.003 (2)	0.0072 (18)	−0.0039 (18)
C7	0.055 (2)	0.0415 (19)	0.033 (2)	0.0007 (18)	0.0055 (17)	−0.0010 (16)
C8	0.0410 (19)	0.047 (2)	0.0307 (19)	−0.0056 (17)	−0.0004 (15)	−0.0031 (16)
C9	0.061 (2)	0.054 (2)	0.040 (2)	0.004 (2)	0.0092 (19)	−0.0026 (19)
C10	0.079 (3)	0.044 (2)	0.049 (3)	0.008 (2)	−0.001 (2)	0.0016 (19)
C11	0.0353 (18)	0.051 (2)	0.036 (2)	−0.0043 (17)	0.0016 (15)	0.0027 (17)
C12	0.048 (2)	0.054 (2)	0.042 (2)	−0.0058 (19)	0.0026 (17)	−0.0002 (19)
C13	0.047 (2)	0.049 (2)	0.066 (3)	−0.0046 (19)	−0.003 (2)	0.015 (2)
C14	0.038 (2)	0.083 (3)	0.046 (3)	−0.003 (2)	0.0025 (18)	0.019 (2)
C15	0.053 (2)	0.084 (3)	0.036 (2)	−0.005 (2)	0.0055 (18)	0.004 (2)
C16	0.054 (2)	0.061 (2)	0.038 (2)	−0.003 (2)	0.0090 (18)	−0.0001 (19)
C17	0.054 (3)	0.104 (4)	0.063 (3)	−0.001 (3)	0.002 (2)	0.037 (3)
C18	0.070 (3)	0.064 (3)	0.039 (2)	−0.009 (2)	0.004 (2)	−0.001 (2)
C19	0.070 (3)	0.072 (3)	0.070 (4)	−0.009 (3)	0.021 (3)	0.015 (3)
C20	0.115 (4)	0.053 (3)	0.035 (2)	−0.015 (3)	−0.012 (3)	0.006 (2)
Cl1	0.0927 (8)	0.0514 (6)	0.0534 (7)	0.0033 (6)	0.0018 (6)	0.0077 (5)
Cl2	0.0760 (7)	0.0845 (8)	0.0583 (7)	0.0128 (7)	0.0199 (6)	0.0173 (6)
Cl3	0.0560 (6)	0.0860 (8)	0.0501 (6)	−0.0079 (6)	0.0026 (5)	0.0116 (6)
Cl4	0.0604 (6)	0.0569 (6)	0.0644 (7)	0.0064 (5)	0.0020 (5)	0.0076 (5)
Hg1	0.06837 (13)	0.05743 (12)	0.06077 (13)	−0.00271 (9)	0.01554 (9)	0.00682 (9)
N1	0.0541 (19)	0.0468 (18)	0.0357 (18)	−0.0079 (16)	0.0010 (15)	0.0042 (14)
N2	0.198 (6)	0.069 (3)	0.038 (3)	0.018 (4)	0.000 (4)	−0.001 (2)
N3	0.060 (2)	0.064 (2)	0.0296 (18)	−0.0103 (17)	0.0025 (15)	0.0118 (16)
N4	0.106 (4)	0.066 (3)	0.053 (3)	0.000 (3)	0.034 (2)	0.011 (2)

Geometric parameters (Å, º) top

C1—N2	1.332 (9)	C12—H12	0.9300
C1—C2	1.332 (9)	C13—C14	1.379 (6)
C1—H1	0.9300	C13—H13	0.9300
C2—N1	1.346 (6)	C14—C15	1.379 (6)
C2—H2	0.9300	C14—C17	1.513 (6)
C3—N2	1.302 (8)	C15—C16	1.381 (6)
C3—N1	1.316 (5)	C15—H15	0.9300
C3—H3	0.9300	C16—H16	0.9300
C4—N1	1.459 (5)	C17—N3	1.476 (5)
C4—C5	1.504 (5)	C17—H17A	0.9700
C4—H4A	0.9700	C17—H17B	0.9700
C4—H4B	0.9700	C18—C19	1.332 (6)
C5—C6	1.379 (6)	C18—N3	1.359 (5)
C5—C10	1.383 (6)	C18—H18	0.9300
C6—C7	1.382 (5)	C19—N4	1.329 (7)
C6—H6	0.9300	C19—H19	0.9300
C7—C8	1.391 (5)	C20—N4	1.307 (7)
C7—H7	0.9300	C20—N3	1.329 (5)
C8—C9	1.382 (5)	C20—H20	0.9300
C8—C11	1.484 (5)	Cl1—Hg1	2.5350 (12)
C9—C10	1.378 (6)	Cl2—Hg1	2.4173 (13)
C9—H9	0.9300	Cl3—Hg1	2.5441 (12)
C10—H10	0.9300	Cl4—Hg1	2.4452 (12)
C11—C16	1.389 (5)	N2—H21	0.90 (1)
C11—C12	1.398 (6)	N4—H41	0.90 (1)
C12—C13	1.380 (5)

N2—C1—C2	106.8 (6)	C15—C14—C13	118.1 (4)
N2—C1—H1	126.6	C15—C14—C17	121.4 (4)
C2—C1—H1	126.6	C13—C14—C17	120.5 (4)
C1—C2—N1	107.4 (6)	C14—C15—C16	120.9 (4)
C1—C2—H2	126.3	C14—C15—H15	119.5
N1—C2—H2	126.3	C16—C15—H15	119.5
N2—C3—N1	108.1 (5)	C15—C16—C11	121.5 (4)
N2—C3—H3	126.0	C15—C16—H16	119.3
N1—C3—H3	126.0	C11—C16—H16	119.3
N1—C4—C5	112.1 (3)	N3—C17—C14	111.0 (4)
N1—C4—H4A	109.2	N3—C17—H17A	109.4
C5—C4—H4A	109.2	C14—C17—H17A	109.4
N1—C4—H4B	109.2	N3—C17—H17B	109.4
C5—C4—H4B	109.2	C14—C17—H17B	109.4
H4A—C4—H4B	107.9	H17A—C17—H17B	108.0
C6—C5—C10	118.4 (4)	C19—C18—N3	107.4 (4)
C6—C5—C4	120.5 (4)	C19—C18—H18	126.3
C10—C5—C4	121.1 (4)	N3—C18—H18	126.3
C5—C6—C7	121.0 (4)	N4—C19—C18	107.3 (5)
C5—C6—H6	119.5	N4—C19—H19	126.3
C7—C6—H6	119.5	C18—C19—H19	126.3
C6—C7—C8	120.6 (4)	N4—C20—N3	108.1 (4)
C6—C7—H7	119.7	N4—C20—H20	126.0
C8—C7—H7	119.7	N3—C20—H20	126.0
C9—C8—C7	118.2 (3)	Cl2—Hg1—Cl4	127.87 (4)
C9—C8—C11	121.3 (3)	Cl2—Hg1—Cl1	105.61 (4)
C7—C8—C11	120.5 (3)	Cl4—Hg1—Cl1	111.72 (4)
C10—C9—C8	121.0 (4)	Cl2—Hg1—Cl3	108.24 (5)
C10—C9—H9	119.5	Cl4—Hg1—Cl3	98.13 (4)
C8—C9—H9	119.5	Cl1—Hg1—Cl3	102.18 (4)
C9—C10—C5	120.9 (4)	C3—N1—C2	108.1 (4)
C9—C10—H10	119.5	C3—N1—C4	126.3 (4)
C5—C10—H10	119.5	C2—N1—C4	125.6 (4)
C16—C11—C12	117.2 (4)	C3—N2—C1	109.7 (5)
C16—C11—C8	121.3 (3)	C3—N2—H21	129 (5)
C12—C11—C8	121.5 (3)	C1—N2—H21	121 (5)
C13—C12—C11	120.7 (4)	C20—N3—C18	107.5 (4)
C13—C12—H12	119.6	C20—N3—C17	125.5 (4)
C11—C12—H12	119.6	C18—N3—C17	127.0 (4)
C14—C13—C12	121.5 (4)	C20—N4—C19	109.7 (4)
C14—C13—H13	119.2	C20—N4—H41	123 (4)
C12—C13—H13	119.2	C19—N4—H41	127 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21···Cl1ⁱ	0.90 (1)	2.25 (2)	3.134 (5)	170 (7)
N4—H41···Cl3ⁱⁱ	0.90 (1)	2.45 (4)	3.168 (5)	137 (5)

Symmetry codes: (i) −x+1, y+1/2, −z−1/2; (ii) x−1, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	(C₂₀H₂₀N₄)[HgCl₄]
M_r	658.79
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.9318 (18), 15.347 (3), 16.840 (3)
β (°)	92.62 (3)
V (Å³)	2306.0 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	7.15
Crystal size (mm)	0.24 × 0.23 × 0.22

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.280, 0.306
No. of measured, independent and observed [I > 2σ(I)] reflections	22111, 5260, 3913
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.068, 1.03
No. of reflections	5260
No. of parameters	269
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.98, −0.94

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21···Cl1ⁱ	0.90 (1)	2.245 (18)	3.134 (5)	170 (7)
N4—H41···Cl3ⁱⁱ	0.90 (1)	2.45 (4)	3.168 (5)	137 (5)

Symmetry codes: (i) −x+1, y+1/2, −z−1/2; (ii) x−1, −y+3/2, z+1/2.

Acknowledgements

The authors thank the Project of Innovation Service Platform of Heilongjiang Province (PG09J001) and Heilongjiang University for supporting this work.

References

Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhu, H.-F., Zhao, W., Okamura, T., Fei, B.-L., Sun, W.-Y. & Ueyama, N. (2002). New J. Chem. 26, 1277–1279. Web of Science CSD CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page m1756

https://doi.org/10.1107/S1600536811047374

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1,1′-[(Bi­phenyl-4,4′-di­yl)bis­­(methyl­ene)]di-1H-imidazol-3-ium tetra­chlorido­mercurate(II)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

1,1′-[(Biphenyl-4,4′-diyl)bis(methylene)]di-1H-imidazol-3-ium tetrachloridomercurate(II)